Ultimate Reading List for Gamblers

The Greatest Gambling Story Ever Told: A True Tale of Three Gamblers, The Kentucky Derby, and the Mexican Cartel
by Mark Paul
The title of this book is obviously somewhat tongue-in-cheek. The storyline revolves around a filly entered into the 1988 Kentucky Derby (kind of like, A Day at the Derby). The inexperienced racehorse, Winning Colours, had very promising form, but was a complete outsider. Three fun-loving and risk-taking punters decided she could be a winner and placed large bets on her at a racetrack in Tijuana, Mexico. Unbeknown to them, the bookies were suspected members of a drug cartel and when this rank outsider won the Derby, the three had to think of a way to claim their winnings without becoming victims of the hostile criminals. Riskiest bet ever?

Bringing Down the House: The Inside Story of Six MIT Students Who Took Vegas for Millions
by Ben Mezrich
The book is the true story of an MIT professor who tutored his students in a Blackjack count-carding strategy that would allow them to take Las Vegas casinos to the cleaners, and they did. Although the book is classified as non-fiction, it is alleged that it contains a lot of fictitious elements, and that some incidents were greatly exaggerated. The book was adapted into the movies 21 and The Last Casino.
What is for real is that various MIT teams won an awful lot of money before the casinos devised ways of shutting them down.

The Biggest Bluff: How I Learned to Pay Attention, Master Myself, and Win
by Maria Konnikova
This book explores a gambler’s psychology ¬– specifically poker players. Author and psychologist Maria Konnikova provides insight into how she was able to predict human behavior which gave her the edge at the poker table.
She had won over $300,000 at the time of publishing, but this figure is growing as she continues to sit at live poker tables and beat her opponents. Konnikova continues to work as a psychologist, researcher and writer, keeping poker as a (lucrative) hobby. From a complete poker novice to one of the most notable women in the game, her achievement is admirable (and hopefully can be emulated).

Fortune’s Formula
by William Poundstone
In 1956, two scientists at the Bell Telephone Company, Claude Shannon and John L. Kelly Jr., decided they needed to come up with a get-rich-quick scheme. They started digging into gambling, stock investing and information theory, and created the “Kelly criterion,” or as it became known – the “Fortune’s Formula.”
Shannon and Kelly tested their theories on everything from Las Vegas blackjack and roulette to Wall Street. Every time, they would end up winning. Their investment strategy would later even be picked up by world-renowned investor, Warren Buffet. Whether you’re into sports betting or casino games, or even the stock market, Fortune’s Formula may just the ticket to help you onto a winning streak.

Soccernomics
by Simon Kuper
Kuper used the 2018 World Cup as an opportunity to find a pattern and devise a strategy that would allow him to win more than he would lose on sports betting. The author argues that each sporting event is unique and therefore it must be studied individually before one places bets. The book doesn’t offer easy solutions, but observing specific events in a game, and in a specific season, could lead to a successful sports betting strategy. To illustrate the futility of predicting outcomes, Kuper self-deprecatingly admits that his wife ended up outscoring him without any scientific knowledge or a deeper understanding of soccer betting! However, the book still delivers quite a few useful pointers.

A Man for All Markets: From Las Vegas to Wall Street, How I Beat the Dealer and the Market
by Edward O. Thorp
Thorp is a mathematician who taught himself to count cards in blackjack, predict stock market patterns and turn his understanding of how the world works into making his fortune. The author has earned $800 million on betting, gambling, and trading. He argues that personal wealth is not always predicated on chance, citing numerous real-life examples to prove his point.
Thorp thinks it all comes down to education; he has spent considerable time studying mathematical constants, patterns, and accumulating non-specialist knowledge that helped him make the right calls in the long-term. (This is all well and good, but what of us poor non-mathematically minded folks?)

Thinking in Bets: Making Smarter Decisions When You Don’t Have All the Facts
by Annie Duke
Duke who sets out to unpack what is involved in making betting decisions and how you can try and produce reliable outcomes with imperfect information. The New York Times described Thinking in Bets as a blueprint for modern investing (investing in the stock market is very much a betting game). Like other great books about gambling, Thinking in Bets approaches gambling from different angles, including behavioral, psychological and business strategies. The book therefore offers an insightful and holistic approach to a fascinating subject.

Blood Aces: The Wild Ride of Benny Binion, the Texas Gangster Who Created Vegas Poker
by Doug J. Swanson
Lester Ben Binion was a Vegas gambling icon, but also a career criminal, a onetime mob boss and convicted murderer. Due to poor health, he never attended school but traveled around with his horse trader father. It was on these trips that he learnt to gamble, many years later opening a business in Las Vegas’s Glitter Gulch – Binion’s Horseshoe casino. While hardly a model citizen, Binion achieved recognition by instituting one of gambling’s biggest and most enduring drawcards: The World Series of Poker. Although he considered himself not very good at poker, preferring organizing games, Binion was posthumously inducted into the Poker Hall of Fame in 1990.